Has anyone made the jump to $uper High end and were disappointed?

Over the years I've been a "serial monogamist" audiophile, usually changing out one piece at a time when doing upgrades.
I have a friend who has a walk-in closet full of "spare" components and when he & his wife "downsized", let me know that the closet was filled with items which disappointed him.
I have been very fortunate, swapping out one piece at a time, and having a dealer I can trust (who has turned down sales when he thought the item I was interested in would not have worked out for me), and with each new piece, have enjoyed an improvement.

Ayon Audio (USA Tube Audio) has classified ads here on audiogon for $25,000 amps (plus other items lower in price). There must be a decent market for such since the ads are everywhere here. I purchase items blind thru the internet since there’s nothing, outside of HT gear, locally to hear in person. Of course, I always make sure there is a good return policy. With that, the stuff I buy is $4000 and under.

I wonder how disappointed a dealer would be to have someone purchase such a high priced (the $25,000 Ayon amp) item only to have it returned. Plus, how cooperative the dealer would be. That’s $25,000 anyway you look at it (a lot of money). I guess that’s the waters the dealer chose to swin in.

Some of the high priced items, like D’agostino, are beautiful to look at and I am sure they sound fantastic

I've never heard Ayon sound good but have heard D'Agostino sound phenomenal. The lesson here is that the sound is in the ear of the beholder. What is most important is how it sounds to YOU.

Spending more $$$ is no guarante for better sound. If you make smart choices along your personal audi journey you will be able to enjoy what you love even more. A higher resolving system can be more rewarding BUT it can also make things worse when you suddenly hear a weak link that was burried before. Working on each weak link can be very rewarding when you manage to achieve improvements. It is like an endless very personal puzzle. And I agree with Robert Harley that the better (not necessarily more expensive) the system gets the larger the reward from small improvements. The oposite of diminishing returns is what happens, when the resolution of your system allows you to hear a significant difference just by changing a minor component. Just throwing big $$$ at it does not at all guarantee satisfaction!

Throwing - no, but super sound is expensive even if you buy used. Let's not fool ourselves.